5. Gangs of New York (2002)

LD’s first of many collaborations with the legendary Martin Scorsese followed DiCaprio as an orphaned boy of an Irish immigrant in Civil War-era New York City. He shared the screen and held his own among the likes of Daniel Day-Lewis, Liam Neeson, Jim Broadbent, John C. Reilly, Brendan Gleeson and Cameron Diaz.